Copolymers of 2‐hydroxyethylmethacrylate and <i>N</i>‐maleoylglycine: Synthesis, characterization, and swelling behavior

Jeria, Manuel; Pizarro, Guadalupe del C.; Marambio, Oscar G.; Huerta, Margarita; Valencia, Paulina; Rivas, Bernabé L.

doi:10.1002/app.22258

Cited by 6 publications

(5 citation statements)

References 19 publications

(5 reference statements)

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“…On the other hand, hydrophobic methyl groups in the polymer matrix ensure hydrolytic stability and mechanical strength. Moreover, P-HEMA is inert to many chemicals, resistant to degradation, thermally stable, and has good mechanical properties as an SCL material due to cross-linking of the chains [ 11 , 12 , 13 , 14 , 15 ]. The main disadvantage of pure P-HEMA hydrogels in ophthalmologic applications is low equilibrium water content (EWC) of only 38% by mass.…”

Section: Introductionmentioning

confidence: 99%

Molecular Dynamics Simulation of Hydrogels Based on Phosphorylcholine-Containing Copolymers for Soft Contact Lens Applications

Filipecka-Szymczyk,

Makowska-Janusik,

Marczak

2023

Molecules

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The structure and dynamics of copolymers of 2-hydroxyethyl methacrylate (HEMA) with 2-methacryloyloxyethyl phosphorylcholine (MPC) were studied by molecular dynamics simulations. In total, 20 systems were analyzed. They differed in numerical fractions of the MPC in the copolymer chain, equal to 0.26 and 0.74, in the sequence of mers, block and random, and the water content, from 0 to 60% by mass. HEMA side chains proved relatively rigid and stable in all considered configurations. MPC side chains, in contrast, were mobile and flexible. Water substantially influenced their dynamics. The copolymer swelling caused by water resulted in diffusion channels, pronounced in highly hydrated systems. Water in the hydrates existed in two states: those that bond to the polymer chain and the free one; the latter was similar to bulk water but with a lower self-diffusion coefficient. The results proved that molecular dynamics simulations could facilitate the preliminary selection of the polymer materials for specific purposes before their synthesis.

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Section: Introductionmentioning

confidence: 99%

Molecular Dynamics Simulation of Hydrogels Based on Phosphorylcholine-Containing Copolymers for Soft Contact Lens Applications

Filipecka-Szymczyk,

Makowska-Janusik,

Marczak

2023

Molecules

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“…Hydrogels generated from HEMA are capable to adsorb from 10% to 600% of water in relation to the dry weight (xerogel). This occurs due to the interaction between hydrophilic group (OH -) of HEMA and the water molecules, which generates hydrogen bonds that allow its absorption and produce swelling [12,13]. On the other hand, in literature it has been described that crosslinked polymers that are composed of acrylic acid (AA) monomers [14,15], N-vinylpyrrolidone (NVP) [16,17], and itaconic acid (IA) [18,19], also possess a high hydration capacity due to the functional groups that have in its molecular structure, generating proper hydrophilicity.…”

Section: Introductionmentioning

confidence: 99%

Hydrogels Based on 2-Hydroxyethyl Methacrylate: Synthesis, Characterization and Hydration Capacity

Oyarce

Pizarro

Oyarzún

et al. 2020

J. Chil. Chem. Soc.

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In the present work, three hydrogels of poly(2-hydroxyethyl methacrylate-co-itaconic acid), p(HEMA-co-IA), poly(2-hydroxyethyl methacrylate-co-acrylic acid), p(HEMA-co-AA) and poly(2-hydroxyethyl methacrylate-co-(1-vinyl-2-pyrrolidone)), p(HEMA-co-NVP) were prepared by free radical polymerization in aqueous solution (1:1 monomer mole ratio) using ammonium persulfate as initiator and N,N´-methylenebisacrylamide as crosslinking agent at two different amount (0.3 and 0.9 mol%). The obtained hydrogels were characterized by Fourier transform infrared spectroscopy (FT-IR), which allowed to verify the structural composition. Thermal analysis of the hydrogels was carried out by thermogravimetric analysis (TGA). In addition, hydration capacity (U%) was studied at different experimental conditions such as: time, pH, concentrations of interfering salts (KCl, NaCl and LiCl). The results showed a good polymerization yield (95%). FTIR characterization shows the absorption bands of the functional groups of copolymers. TGA exhibited the characteristic thermal stability of this type of hydrogels. The presence of comonomer AI, AA or NVP in copolymer determine the thermal behavior. Hydration experiments revealed a higher U% in copolymer containing more carboxylic acid groups. The maximum U% values in water were 400% and 250% for p(HEMA-co-AI) and p(HEMA-co-AA), respectively. For P(HEMA-co-NVP) a maximum of U% value was only 74% in water. The effect of interferent salts affects the hydration capacity decreasing U% when the concentration of salts increase.

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“…The reason for this sharp phase transition is a good balance between hydrophilic and hydrophobic interactions in the polymer [17] . It undergoes a temperature induced collapse from an extended coil into a globule structure, a transition revealed on the macroscopic scale by a sudden decrease of the degree of swelling of poly(NIPAAm) gels [18][19][20][21][22][23][24][25][26][27][28][29][30][31] . Raising the temperature of an aqueous poly(NIPAAm) solution above the LCST causes a coil-to-globule transition, followed by a phase separation.…”

Section: Introductionmentioning

confidence: 99%

“…We have previously published [29][30][31] the synthesis and swelling properties of hydrogels from functional vinyl monomers. These systems showed that the copolymers containing acrylic acid and acrylamide derivative moieties are very sensitive to stimulus as pH, temperature, ionic strength, and copolymer composition.…”

Section: Introductionmentioning

confidence: 99%

Hydrogels Based on (Dimethylamino)ethylacrylate (Dmaea) and N,n'-Dimethylacrylamide (Nndmaam): Synthesis, Characterization, and Swelling Behavior

Pooley

Rivas

Pizarro

2013

J. Chil. Chem. Soc.

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Hydrogels of 2-(dimethylamino)ethylacrylate (DMAEA) with N,N′-dimethyl acrylamide (NNDMAAm) were synthesized by solution free-radical polymerization at different feed mol ratios. These copolymers were completely water-insoluble. Polymers were characterized by elemental analysis, FT-IR spectroscopy, thermogravimetric analysis (TGA), and scanning electron microscopy (SEM). The monomer reactivity ratios were determined by Kelen-Tüdos method. According to that, the monomer reactivity ratios for poly(DMAEA-co-NNDMAAm) were r 1 = 0.288 (M 1 =DMAEA) and r 2 = 1.460 (M 2 =NNDMAAm), (r 1 x r 2 = 0.419). Low critical solution temperatures (LCST) values of hydrogels are around 60°C, which was significantly higher than that poly(NIPAAm) and increased with increasing of hydrophilic DMAEA unit content in the copolymers. The hydrogels achieved a water-absorption value of 188 g of water/g of dry polymer (xerogel) in distilled water. Effects of time, temperature, pH, salt concentration, cross-linking concentration, and solvent polarity on the water absorption were studied. Experimental results indicated that the copolymer poly(DMAEA-co-NNDMAAm) with a feed mol ratio 2:1 presents the best swelling properties.

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Copolymers of 2‐hydroxyethylmethacrylate and N‐maleoylglycine: Synthesis, characterization, and swelling behavior

Cited by 6 publications

References 19 publications

Molecular Dynamics Simulation of Hydrogels Based on Phosphorylcholine-Containing Copolymers for Soft Contact Lens Applications

Molecular Dynamics Simulation of Hydrogels Based on Phosphorylcholine-Containing Copolymers for Soft Contact Lens Applications

Hydrogels Based on 2-Hydroxyethyl Methacrylate: Synthesis, Characterization and Hydration Capacity

Hydrogels Based on (Dimethylamino)ethylacrylate (Dmaea) and N,n'-Dimethylacrylamide (Nndmaam): Synthesis, Characterization, and Swelling Behavior

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